The Digital Transformation Playbook
Kieran Gilmurray is a globally recognised authority on Artificial Intelligence, cloud, intelligent automation, data analytics, agentic AI, and digital transformation.
He has authored three influential books and hundreds of articles that have shaped industry perspectives on digital transformation, data analytics, intelligent automation, agentic AI and artificial intelligence.
𝗪𝗵𝗮𝘁 does Kieran do❓
When I'm not chairing international conferences, serving as a fractional CTO or Chief AI Officer, I’m delivering AI, leadership, and strategy masterclasses to governments and industry leaders.
My team and I help global businesses drive AI, agentic ai, digital transformation and innovation programs that deliver tangible business results.
🏆 𝐀𝐰𝐚𝐫𝐝𝐬:
🔹Top 25 Thought Leader Generative AI 2025
🔹𝗧𝗼𝗽 𝟱𝟬 𝗧𝗵𝗼𝘂𝗴𝗵𝘁 𝗟𝗲𝗮𝗱𝗶𝗻𝗴 𝗖𝗼𝗺𝗽𝗮𝗻𝗶𝗲𝘀 𝗼𝗻 𝗚𝗲𝗻𝗲𝗿𝗮𝘁𝗶𝘃𝗲 𝗔𝗜 𝟮𝟬𝟮𝟱
🔹Top 50 Global Thought Leaders and Influencers on Agentic AI 2025
🔹Top 100 Thought Leader Agentic AI 2025
🔹Top 100 Thought Leader Legal AI 2025
🔹Team of the Year at the UK IT Industry Awards
🔹Top 50 Global Thought Leaders and Influencers on Generative AI 2024
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🔹Best LinkedIn Influencers Artificial Intelligence and Marketing 2024
🔹Seven-time LinkedIn Top Voice.
🔹Top 14 people to follow in data in 2023.
🔹World's Top 200 Business and Technology Innovators.
🔹Top 50 Intelligent Automation Influencers.
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🔹Global Intelligent Automation Award Winner.
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𝗖𝗼𝗻𝘁𝗮𝗰𝘁 my team and I to get business results, not excuses.
☎️ https://calendly.com/kierangilmurray/30min
✉️ kieran@gilmurray.co.uk
🌍 www.KieranGilmurray.com
📘 Kieran Gilmurray | LinkedIn
The Digital Transformation Playbook
Fractional Power For Growing SMEs
What if you could borrow a battle-tested executive exactly when you need them and only for as long as it takes to move the needle? We pull back the curtain on fractional leadership for SMEs, focusing on the people side of change where complexity lives and value compounds.
TLDR / AT A Glance:
• What fractional leadership is and why it matters for SMEs
• Complexity of people versus utility of technology
• Why “digital transformation” distracts from systems and culture
• How empowerment beats command and control
• Common SME patterns and how to fix them
• Product thinking for HR and quick, measurable wins
• What makes a great fractional leader
• How to choose and work with a fractional chief
Across a fast-moving conversation, we define what a fractional C‑suite leader actually does and why it’s not a cheaper helpdesk. Think senior judgment on tap: diagnosing root causes, running smart experiments, and owning outcomes.
We challenge the myth of “digital transformation” by reframing technology as a utility and putting human systems front and centre. AI and automation clear the noise; empowered teams create the signal. That means unlearning command and control, pushing decisions closer to the market, and building lightweight structures that turn information into action.
You’ll hear concrete patterns from the SME trenches: overcontrol driven by tight budgets, underused tech, and fads that burn cash without impact.
We share how product thinking applies to HR - test, measure, iterate and what early proof points look like when you are fixing retention, engagement, and capability. For practitioners eyeing fractional work, we cover the mindset shift from corporate to owner-led businesses, the breadth required across HR disciplines, and why emotional intelligence is as critical as technical depth.
For founders choosing a fractional chief, we offer a simple playbook: verify track record, align on outcomes, insist on execution, and value a partner who can challenge without breaking trust.
If you want senior expertise without the full-time price tag and you’re ready to trade decks for delivery this conversation maps the path.
Subscribe, share with a fellow leader who needs this lens, and leave a review with the one capability you’d rent first.
𝗖𝗼𝗻𝘁𝗮𝗰𝘁 my team and I to get business results, not excuses.
☎️ https://calendly.com/kierangilmurray/results-not-excuses
✉️ kieran@gilmurray.co.uk
🌍 www.KieranGilmurray.com
📘 Kieran Gilmurray | LinkedIn
🦉 X / Twitter: https://twitter.com/KieranGilmurray
📽 YouTube: https://www.youtube.com/@KieranGilmurray
📕 Want to learn more about agentic AI then read my new book on Agentic AI and the Future of Work https://tinyurl.com/MyBooksOnAmazonUK
My name is Kieran. I'm a globally recognized authority in AI automation and digital transformation. What I'm recognizing in the market is that companies now want access to expertise like mine and others, where they may not have the budget. They may be at that particular when I say budget, we're talking about budget to pay someone with 10, 20, 30 years experience, an annual recurring salary, but they're not quite there yet. In other words, they're scaling up or they recognize the need, but they don't know where to go to. Now there is a growing concept called fractional support, fractional CTOs, fractional chief AI officers, and fractional chief HR officers. Today I have Barry Flack, an award-winning global HR executive with three decades of frontline experience in senior leadership gigs, a true technophile. He's operated as an advisor to a variety of HR tech startups and since 2018 works primarily in the SME sector as a fractional HR leader, helping CEOs create great workspaces. I'm delighted to have him today. And Barry and I are going to talk about what it means to be fractional. Welcome, Barry. How are you?
Barry Flack:Thank you, Karen. Yep, look, I am great on this uh somewhat dark uh morning we're uh both talking on.
Kieran Gilmurray:So all good. Excellent. Uh look, let's jump straight in, Barry. What exactly is a fractional C-suite executive? And why do we describe it as a game changer for SMEs?
Barry Flack:Yeah, look, it's um I've been in this game, as you've rightfully dictated, for uh for quite a long time. Uh getting myself involved in lots of different types and variations. Fractional put simply is about taking those like ourselves at a senior experienced C-suite level and allowing our SME sector to get what they've never had before, which is that level of experience, that level of expertise, that ability to plug somebody in um and tackle hugely complex issues, uh, none more complex than the world of people.
Kieran Gilmurray:And is this uh what kind of problems are you solving for? Is this a cheap method to get HR support? Or are we talking about something more complex, more strategic, bigger than the day-to-day?
Barry Flack:Yeah, look, this uh interaction is about dealing with complexity. And look, you know, what definition does that mean for me? Um, that means people who are utterly unpredictable. It means markets and external forces that are equally unpredictable, and we've been through enough of those in the last couple of decades. We've still got the backdraft of COVID, you know, we had Brexit, we had financial global crises. Um, the secret or not so secret is to sort of accept that those things are unpredictable. So for people like myself, it isn't a traditional I as a C-suite have got um a problem diagnosed, it's this as a rollout, technology, people, learning programs, and I want you to come in and manage that. That's a very different thing. This is an acceptance that says I don't have this competence, I don't have this capability, and I don't really have either the time or the expertise to deal with what I typically am doing in this people space because I'm spending a lot of money. Um, but I want you to come in, take the gears, develop it using that word strategically. And I think the difference also, and we know SME, look, it's not a place where there are big teams, big budgets. So you've got to roll your sleeves up, you've got to execute, you've got to make change happen. So it's very much uh a unique, it's not about taking part-time. Let's all sit around and talk, and I'm only here on a Monday. This is grab it, make a difference, um, be focused on outcomes, but convince me what those outcomes are because I don't know how to handle this.
Kieran Gilmurray:Yeah, so that little bit of expertise that they don't enjoy on a daily basis and probably don't need seven days a week just at this stage. Now, you mentioned about you know the unexpected, and I think the unexpected is becoming more expected, it's more regular, which is extraordinary. But one thing we look at is the hype curves suggesting that AI will now change the world for everyone, never mind SMEs. Uh, but you suggested before there's no such thing as digital transformation. What do you actually mean? And how are you advising SMEs that there is no such thing as digital transformation?
Barry Flack:Yeah, look, I have um now seen the entire journey, I think, from the from literally taking what we used to file in the cabinet, you know, on and categorizing our databases through an enormous amount of hype curves, through yes, you know, SAS arriving, through a lot of functionality. And and look, that's what it is. It's the world of complicated. It's the incredibly clever people, but who grab all of the headlines, you know, who write the books, who show us the Boston dynamics. Um, they are ultimately, you know, a utility, an increasingly important and an increasingly, you know, sexier agenda than the complexity of people. So we've always had the backstory of getting technology over rated and people underrated in terms of our impact on it. So we still live in that particular curve. The technology in enabling automation, and I think that's still where we are, regardless of what we call digital transformation. We're still very much early adopters in SME around that AI piece. This is about actually the impact it has on people, the personal journey they go through, the ability they have to have that free time to do what, frankly, has always moved the DAO, their thoughts, their ideas, their innovation, their ability to work together on a problem, their ability to be close to the market and spot all of that complexity. Uh, no machine will do that. It'll support us. It's a utility. So there is no digital transformation, it's just a utility that is getting better. But what it does is it takes on a life that clearly still overwhelms the important agenda, which is people, systems, and how we organize in this world of chaos.
Kieran Gilmurray:So, if as you suggest, people are infinitely complex, what do the best SMEs do to allow people to thrive?
Barry Flack:First and foremost, all of them need to go through their own personal journey of realizing that what we did for about 100 years, uh, what we call command and control, uh is dead, does not work in our market. So the idea that you will unlearn lots of bad habits that frankly we have taught the C-suite for far too long, where control um, and typically a HR function that's been part of that control agenda is now given up by a recognition that people as close to their market um is about empowering them. It's about turning the old um pyramid upside down and understanding where the executive sits uh in amongst all of that. It's about what levels of capability and understanding do you go through in understanding the market you serve, in organizing around that? How do you place the right level of insight and information? Well, then going back to our friends in technology, you utilize the stuff that comes in, you categorize it, and you give it a force for good in decision making. So a lot of this is about recognizing that lazy tropes, like people who need the stick, people who need the overwhelming carrot, people ultimately want to come and be heard, be listened to, be valued, and the best SMEs create the environment that allows people down into the organization to use their brain, freed up from the mundane, that once again our technology will help uh embrace and do better.
Kieran Gilmurray:So, what kind of patterns then do you come across in your work with SMEs that differ from large corporates? Who've maybe talked about some of these concepts for a while but never quite delivered them?
Barry Flack:Yeah, look, uh the obvious recognition is we're in an environment where every pound counts, you know, without investment issues there. We have, and I'll be absolutely on, we have a just good enough philosophy at times in how we run it. And that tends to be back down in cost parameters. This is what I can pay for in doing that particular role. This is what I will get. That's just what it is and how it looks. So going back to fractional, you know, that's the groundbreaker in changing that paradigm on it. So, you know, patterns in there evolve from a desire with scarce resources to over control, um, to be behind the curve in too much of the technology adoption, to not get the most in relation to some of the investments we make, um, and still the hold into the way we've always worked in success factors in the future.
Kieran Gilmurray:See, this is the kind of thinking that I think has been missing for companies for years. And with respect to you know, incumbent CHROs, they maybe don't get the opportunity to raise their head above the parabet because they're so involved in the day-to-day, you know, and therefore to get that expertise coming in and you know, have someone actually examining the market for them and bringing specialist advice, as you say, not one day a week, but actually rolling your sleeves up and getting things done is so key. So, Barry, if people are thinking of moving into a fractional role, you know, to work with C-suite executives, because this sounds like the fun part of a job, what sort of advice would you give them?
Barry Flack:I think the recognition that uh especially if you've got a big corporate background, that you're dealing with, you know, talented people who just don't talk in that language. You've got business owners, you know, who want a profitable business. So, how do we interpret what might feel like an academic conversation into uh well, what does this mean? How does it manifest itself? How comfortable are you across the spectrum? There's something like 23, 24 established disciplines inside the old HR family from recruitment and training and employee relations. You you've got to have a grasp of all of them. You've got to look at the problem the company has through a very systemic route. Yeah, why are they losing people? Is it about the culture? How are people behaving? Have they over-indexed on engagement? You know, some organizations have gone down the faddish route, spent a lot of money, and have had no return on a lot of things that we've seen post-COVID around well-being and developmental stuff, you know. I mean, so do you bring product thinking in? You know, do you test your hypothesis? Do you not just land it and allow a C-suite to feel they've lost their investment? So the doing piece is you've got to move quickly. You've got to get that proof point. And then I think like finally, for any person professionally coming in, you know, you've got a lot of heavy lifting to do to run that business, to get that message out, to convince a still off-market skeptical, you know, C-suite that this is something worth taking on. You know, we're still at the early stages, fractional numbers. I've been doing this since late 2018. I think we had 2,000 people, you know, swirling around. Those numbers have hit tenfold, 50-fold now. But some of those individuals are still taking a very siloed, you know, focused solution to a big broad problem that exists out there. So it's not for everybody. Um, but like for the business that's out there consuming it, it's a wonderful opportunity to get expertise that was previously beyond reach.
Kieran Gilmurray:Yeah, I suppose that's it, isn't it, though? Because you see a lot of ex-consultants from again the big four or whatever you want to call them, fancying doing a gig where they turn up pontificate, uh suggests there's a magic wand of these things, but it is complex. And again, as you and I know, it's about getting SMEs the results they want, not just giving them some advice and walking away. It's about owning it. So, Barry, just final question. If someone was looking for a really great fractional, what are the sort of things that they should be looking at saying, you know, that's what I need? So again, experience, I'm assuming, is one book, but what else if they've got their criteria to pick an amazing fractional to plug in whatever that is, you know, one, two days a week, a month, or whatever else to allow them to get the results that they require?
Barry Flack:Yeah, look, I think it's the track record of showing that you've got those breadths of skills, and they're the the hard technical ones that we've mentioned, you know, what could be the answer, what could be the way that we explore this. Um, but I think there's also the bit we haven't really spoken about, and that's the level of emotional intelligence, uh, coaching, you know, empathy that goes with this. You know, if you know, people listening remember at the beginning, you know, we talked about unlearning. You know, we challenge, I challenge C-suite to be able to think of how they've always done something. And you've got to put up with people's personal reactions to being told that that doesn't work anymore. You know, they've got their own complexities that they're handling. But the very best C-suite are the ones who get the relationship, is also about not knowing. We've brought you in, you've got an expertise, you're challenging us, it's a bit painful, but actually we've reached a point where if we keep doing what we've done, we'll just get those same results and we need a breakout piece. So, you know, coming in, as you say, producing the decks, leaving them there, you know, just not following through and executing, and having a good, you know, relationship with the people at the C-suite and in the organization, um, you know, is all part of the success criteria, or it just becomes another field project.
Kieran Gilmurray:So I really like that, you know. So from a couple of levels, and let me draw one or two lessons that I've learned out of this. So it is about the track record and the willingness to explain and to challenge and bring the expertise and bring the muscle, for one of a better phrase, as opposed to producing a deck and working or walking away. But also, as you described there a second ago, it's about that executive team knowing that they brought you in for a particular reason, and that isn't to tell them that they're wonderful, because if they've identified the need, you know, where there is a problem, they know they need to fix it, and therefore getting uncomfortable is the reason why you're bringing in this fractional expertise. So also, it's not just that, but if companies are at a particular point in time where they're ready to scale and ready to grow, but maybe they don't have the budget to pay for someone, you know, for a full 12 months a year, plus everything that that brings with it the pensions, the holidays, the sickness, and everything else, but they need to plug in a certain amount of expertise on a regular recurring basis. Going to allow them to, for one of a better phrase, bring someone in like you who has seen round corners, been there, done that, and can guide them from making a whole host of mistakes or in indeliberate missteps. Then that's another core reason why you might want to bring in a fractional. Barry, if people want to find out a little bit more about you and fractional, how do they go about doing that?
Barry Flack:Yeah, look, I'm pretty active on LinkedIn. Um, I've kicked off a newsletter that's very much geared towards the problems that SMEs have. So certainly subscribe if that's something that's helpful. And anybody looking in who's curious uh about uh the whole issue of fractional as a practitioner, I've got some support collateral that can help them. Uh, and my invite in to talk to people is is always there. I mean, getting more people across the C-suite to do this, to add value, can only be a good thing for us as a you know, as an economy in terms of growth, in terms of doing the right stuff, you know, at a local level at the SME. So catch me there. Uh, I look forward to any follow-up questions. Fantastic.
Kieran Gilmurray:Luke, folks, uh Barry, thank you for chatting to me today. Folks, thank you for listening in as well. Look, to get access to expertise that you couldn't normally get at a cost and a price point and a time of your choosing is an amazing thing. Having been and currently am a fractional, I see the value that this brings. And having worked with Barry, I see the value that he brings as well. Reach out, do get connected, ask the question because this is a skill and service that every company should avail of. Until next time, thank you very much for listening.
Barry Flack:Thank you.